Vacation rentals in Saint Leonard

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Top-rated vacation rentals in Saint Leonard

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Superhost

The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.

Cabin in Lusby

4.92 out of 5 average rating, 218 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Top guest favorite

The exterior of a single-story beach house is visible, featuring white siding and landscaped areas. A stone pathway leads to a cozy outdoor seating area with light cushions. Lush greenery and mature trees are present, contributing to a serene atmosphere.

Home in Lusby

4.99 out of 5 average rating, 229 reviews

Cove Point Cottage with Chesapeake Bay views

Welcome to our beach house, just a block from the Cove Point Beach on the Chesapeake Bay. Start your beach day by grabbing the beach wagon from the shed, loading it up with beach chairs, towels, and your cooler. A short stroll takes you to the beach, where you can spend the day searching for shark teeth and shells or swimming in the bay's refreshing waters. After a day in the sun, rinse off in our outdoor shower. Our shady patio provides the perfect spot to relax and enjoy the evening breeze.

Top guest favorite

The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.

Home in Solomons

5 out of 5 average rating, 104 reviews

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Superhost

A serene waterfront view showcases the Chesapeake Bay, stretching towards the horizon under a clear sky. The shoreline features wooden docks and gentle waves, while quaint homes are seen along the sandy beach. Green trees provide shade in the foreground.

Home in Saint Leonard

4.89 out of 5 average rating, 133 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Top guest favorite

Two light blue Adirondack chairs are positioned on a wooden dock, facing a calm river. The sun sets over the water, casting a warm glow across the surface and creating a serene atmosphere. A weathered wooden table is placed nearby, enhancing the inviting scene.

Guest suite in Lusby

4.98 out of 5 average rating, 357 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

Top guest favorite

An open living space features a vibrant wall art piece and comfortable seating, including a recliner and a sofa. A dining area with four chairs is visible, along with a well-equipped kitchen. Light-colored cabinetry complements the neutral tile flooring, creating a welcoming environment.

Apartment in Lexington Park

4.97 out of 5 average rating, 135 reviews

Serene setting great location surrounded by woods

The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

Top guest favorite

A red umbrella provides shade over a square table with a glass top, accompanied by two cushioned chairs. Lush green grass surrounds the seating area, framed by tall trees and distant views of the water, creating a serene outdoor space.

Apartment in Port Republic

4.96 out of 5 average rating, 224 reviews

Serenity Suite on Chesapeake Bay

Come enjoy our waterfront home on the scenic Calvert Cliffs. Relax by the water under mature shade trees. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails and enjoy dinner on Solomon’s Island. Then open the windows to listen to waves overnight.

Top guest favorite

A wooden dock extends over the water, leading to a sun setting on the horizon. Waves gently lap against the sides, reflecting warm hues of orange and pink as the sky transitions into dusk. Two benches are positioned on the dock, inviting peaceful contemplation.

Loft in Lusby

5 out of 5 average rating, 388 reviews

Chic Loft Retreat | Private Beach & Near Solomons

STAY IN or ADVENTURE OUT Relax in a chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons & Calvert Cliffs. Enjoy your own private above-garage hideaway with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. Our open-concept space, has a bedroom area, bathroom, workspace, living room & kitchen. SMOKE FREE SCENT FREE PET FREE PEANUT FREE We offer an Air Purifier and use only all natural cleaning products.

Top guest favorite

The exterior of the house showcases multiple large windows that invite natural light, with a spacious porch area featuring white outdoor chairs. Colorful flower planters enhance the surroundings, providing a serene setting among greenery.

Home in St. Leonard

4.92 out of 5 average rating, 186 reviews

Cozy Cottage on the Chesapeake Bay

Tranquility supreme. Sit on the terrace and gaze at the Chesapeake Bay. Sandy beach -- just 50 steps from front door; quiet residential area; nearby antiquing & fishing; Only 75 min. from DC. Finish your book or just replenish your spirit. Enjoy. Oh, one more thing — looking for the perfect place for a retreat for your small DC team? Strategic planning will be even more creative and enjoyable when you have the Chesapeake Bay as your muse. Note: This property is for non-smokers.

Top guest favorite

An entryway leads through tall grasses and dunes to a sandy beach covered with colorful umbrellas. The clear blue sky and calm water create a serene setting, while beachgoers enjoy the day in the distance.

Guesthouse in Saint Leonard

4.97 out of 5 average rating, 116 reviews

Studio on the Bay.

This studio apartment is in walking or driving distance to three private beaches in our community. There is 1 bedroom with a queen size bed, spacious bathroom and closet. The living room has a pull out full size bed and a kitchenette. Coffee, teas, beach chairs, are provided. Wanna fish??? Ask Joey about Fish Taxi! Fifteen minutes from Solomons Island (home of the Tiki Bar). An hour or so from DC, Annapolis and Waldorf.

Guest favorite

A wooden staircase illuminated by soft lights leads down to a private dock. Reflections of trees and evening sky are seen on the calm water of St. Leonard Creek. A sailboat is moored at the end of the dock, adding to the serene waterside ambiance.

Cabin in Lusby

4.9 out of 5 average rating, 283 reviews

Peaceful Waterfront Retreat on The Bay

Escape to a serene waterside cabin with a private dock on quiet St. Leonard Creek, just an hour from Washington, DC. This rustic studio offers a cozy retreat for solo travelers, couples, or small families looking for peace and relaxation. Whether you're here to unwind, work remotely, or explore the outdoors, you'll find plenty to enjoy—including two kayaks, two canoes, and stunning waterfront views.

Superhost

A fire pit surrounded by stones contains a gently burning fire. The sandy beach leads to a calm body of water, with a pier extending into the distance. Soft hues of sunset color the sky, providing a serene backdrop to the scene.

Cottage in Saint Leonard

4.84 out of 5 average rating, 125 reviews

Spacious Beachfront Retreat w/Dock

Relax with the whole family at this peaceful place to stay. This charming home features 5 bedrooms and 3 full bathrooms. All bedrooms have a waterfront view. Enjoy watersports - kayaking, fishing, paddle boarding; or relax on the beach by a fire and enjoy the sunset. Bring your jet skis or fishing boat, the marina is 5 miles away.